(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(2H2)acetyl]-2,13,15-trimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 161999
• Molecular Formular: C22H29FO5
• Molecular Mass: 392.4610632
• Monoisotopic Mass: 392.19990225
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)CO)O)C)C)O)F)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: UREBDLICKHMUKA-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β,16β)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione-d5; 9α-Fluoro-16β-methylprednisolone-d5; Betadexamethasone-d5; Flubenisolone-d5; Sch-4831-d5; NCS-39470-d5; Betamethasone-d5

Database IDs

• PubChem SID: 162256134
• PubChem CID: 71313950

CALCULATED PROPERTIES

• Acid pKa: 12.423736
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6815696
• LogD (pH = 7.4): 1.6815655
• Log P: 1.6815697
• Molar Refractivity: 102.4929 cm^3
• Polarizability: 39.61867 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White to Light Yellow Solid
• Melting Point: 233-236°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B327002

Glucocorticoid.

REFERENCES

• Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977)
• Li, A., et al.: Chem. Biol. Interact., 142, 7 (1977)
• Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (1977)
• Rothfuss, A., et al.: Chem. Res. Toxicol., 19, 1313 (1977)